
Vacation rentals with outdoor seating in Chilmark
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Top-rated outdoor seating rentals in Chilmark
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Popular amenities for Chilmark outdoor seating rentals
House rentals with outdoor seating

Modern Marvel in Woods Hole - Walk to town & ferry
We traveled with 4 couples who have know each other since HS, 40 years ago. It was a great home to relax and catch up. The house is lovely and we loved that we each had our full bath! I highly recommend this home and this location.

Sunny, Spacious Vineyard Retreat
Fran's house is lovely, everything one needs for a fabulous stay. She is a very good host - responsive and informative. She lives on the prpoerty but we never saw her. We had a really great stay!!!

Vineyard Haven Walk to Ferry
We totally enjoyed our stay! Our first night we stayed out due to rain but that didnât stop a grand time cooking at home! We had everything we needed to cook in and relax! The accommodations were perfect for the 3 of us with each of our own rooms. We enjoyed the turkeys and all their antics-lol. Thank you for a great place to stay! We will be back!

Waterfront-Kayaks & SUPs-Firepit-Pet OK-Kingbed
Beautifully remodeled home, lovely setting on a large pond. Everything was clean, the kitchen was well stocked. I am an avid cook/home chef and appreciate the decent cookware. So many places have understocked kitchens and wounded cookware. Comfortable King bed. Thoughtfully decorated. Nice quiet neighborhood. We travel with our 13 year old boxer who has traveled the country and we appreciated the one level living. We did not mind being farther from town, we love the wildlife and the beautiful swan swimming on the pond! The host, Benjamin, was easy to get ahold of, though we had no issues with anything at all. The booklet on Salt Crystal that was sent ahead to us was extremely helpful to us! We would definitely stay here again!

Quaint Roomy Ranch
House was very cozy. Nice quiet neighborhood. Beds were very comfortable. I would not hesitate to stay there again.

â Beach â Downtown â Restaurants/Bars â Bike Path
Great location just over 2 miles (3.5 K) from the heart of Edgartown. There is a little bit of road noise per the other reviewers but it minimal, especially at night. The place is very clean and has everything you need for a comfortable stay. We were 4 adults, stayed for 2 nights, and had a vehicle so were able to easily explore the island from this location. Other than breakfast, we ate out (lots of great places to eat on MV) but the kitchen is fully equipped should you choose to eat in. The nearby Stop and Shop grocery store is well stocked.

Beachfront W/ HotTub,Sauna, Pool & Panoramic view
This house was exactly how it was described. As soon as you pull into the drive way you see a gorgeous house. Checking in was a breeze. Gary gave us the pin and we were all set to access the house. The pictures do not do this house justice. Everything was spotless. We felt like we were home. Our host Gary was so sweet and responsive. He created this welcome booklet which helped so much. We couldnât have asked for a better weekend away. We cannot wait to come back and stay at Garyâs house. Thanks Gary for everything!

20-minute walk to Edgartown Village!
We had a wonderful stay at Madisonâs place! The home was fantastic for our family of four. Tastefully decorated, very comfortably laid out, and the kitchen is fully stocked. Madison left a welcome gift that was much appreciated, and proactively communicated throughout our stay. There are a few restaurants and shops within a 5-min walk, and downtown Edgartown is about a mile away. Would 100% stay here again if we come back to MV!
Apartment rentals with outdoor seating

WATERFRONT PENTHOUSE OAK BLUFFS
We spent our anniversary at Leslieâs place and it was a beautiful! The views and location was like no other and we would book again! Leslie was very responsive and even left us some dinner when we came in late from the ferry. The restaurant staff were friendly and it was everything described in the listing. We didnât want to leave!

15 Acres of Open Fields & 15 Minutes to the Beach
We went to stay at Cathleen's for my very first big ticket concert. We were met by her mom Judy who was very kind and helpful. The place was very homely , very clean, had a beautiful garden and the property is stunning! We had a great stay, would go back! And highly recommend!

Taylor's Pharmacy Guesthouse
We had a perfect stay â travelling with a toddler can sometimes be challenging but Debora provided everything we needed to make the stay comfortable (cot, high chair, bath, even cutlery!) and it really felt like a home away from home. The airbnb was spotless, itâs a good location in Fall River walking distance from a playground, parking was super easy, and we loved our stay.

Harbor view apartment, a quick walk from the ferry
Mark's place was exactly how it appeared in photos. Great, walkable location. Easy to get to restaurants on Main St. There's a place to rent bikes just across the street. The stay was comfortable, quiet, and exceeded expectations. Thank you again, Mark!

Main Street on the Park
Beautiful and well-maintained place. We had a minor issue, but Jonas was very proactive in resolving it. Felt right at home.

â Gorgeous Beach Views -- The Sand Dollar Suite
Relaxing girls get away weekend. Amazing views, very walkable and friendly town and beach. (Delicious local ice cream shop- vegan options too!). The perfect place to relax, catch up with friends, and make some delightful memories.

Home by the Sea
This was our second stay and there's a reason we came back! The space is cozy and comfortable - We especially appreciated the easy flexible check in and snacky snacks and coffee. Thank you Norm!

Your Private Garden
We had a lovely time at Mary Aliceâs place. She was incredibly kind, helpful, and responsive before, during and after our stay. Even though we werenât able to meet in person, she made sure we felt welcomed and had what we needed. She also offered flexible checkin/checkout which we didnât end up needing, but it was nice to have as an option! The location is a quiet and cozy neighborhood that offered us privacy but was also walkable to the main street. Many thoughtful touches incorporated into the place - I can tell that she treats her home with so much love and care, and it shows! Would recommend!
Condo rentals with outdoor seating

Short Walk into Town - Nice Comfortable Reasonable
Walkable to all local shops. Unit was clean and the kitchen was fully stocked with all items needed to prepare and enjoy a meal.

Relax....You're on Island Time......
Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.

Crow's Nest Down Town New Bedford.
Phil's place is ideally located in New Bedford for beautiful walks along the pier and throughout the downtown historic district. Close to great restaurants and coffee shops. The crows nest offers the best views of the downtown! Phil was very helpful and responsive. Easy to get checked in and out.

Hidden Hideaway
The location is fabulous and very close to many amenities - coffee, groceries, restaurants and the beach. While it was a small space, it was well laid out, comfortable to be in, very clean and had a respectable kitchen for its small size (which I used). Devon was very proactive and friendly when I asked him about the microwave not working - I had missed that it wasn't plugged in! The condo was very quiet at night even though it is close to a road. I will definitely return to Devon's place should I need to travel there and it is available.

Sunny 2bedroom condo w pool, walk to town
We had a great time at Leahâs place. She is a terrific communicator, immediate responses. She also reached out to share about local fun events that were happening during our stay. So nice! We would definitely stay there again.

Beach Cottage 3nts/4th Free in August,Mashpee MA
Our second visit. We love the place. Quiet but close to great beaches and the Popponesset Marketplace is 2 minutes walk away, with fish restaurants and small stores with necessities (including wine and beer!). A highlight of this visit was sitting on the patio in the morning and 3 times seeing an osprey dive to the pond and catch a fish.

6 Min to Beach - Pool - Private Balcony - Central
My boyfriend and I stayed in this beautiful and quaint condo for a wedding weekend in Dennis and it couldnât have been a more perfect place with a more perfect location!We both felt safe and comfortable immediately upon arrival and loved spending time outside on the porch and enjoying walking around the area! We would both recommend this stay to anyone!

Millie's-Historic New Bedford, 2BR, water views
We had a great six nights here. The space is super cool, well appointed with comfty beds and super soft towels, and was squeeky clean! We enjoyed the roof deck, the views to the waterfront, and the fireplace--and had an exceptional meal at Cork, too! Our stay was a combination of a work trip plus time to explore New Bedford and the SouthCoast and the location was great for both. Having a dedicated parking space was great, too. We would happily return.
Quick stats about vacation rentals with outdoor seating in Chilmark
Total rentals
100 properties
Nightly prices starting at
R2,154Â ZAR before taxes and fees
Total number of reviews
2.5K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
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- Cape Cod
- Mayflower Beach
- Charlestown Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Brown University
- Easton Beach
- Sagamore Beach
- Sandwich Glass Museum
- Roger Williams Park Zoo
- Owen Park Beach
- Point Judith Country Club
- Oakland Beach
- Blue Shutters Beach
- Onset Beach
- Ninigret Beach
- Inman Road Beach
- South Shore Beach
- Nickerson State Park
- Fort Adams State Park
- Second Beach
- Oyster Harbors Beach